The saga of NSA contractor Reality Winner has taken one more step toward conclusion with her transfer from the federal prison to a residential re-entry home, also in Texas. As readers will recall, we last visited Winner’s situation in February 2020 when her lawyer petitioned the President for clemency. Her request was not granted, and she was left to serve out the remainder of her sentence.

Her current transition is not a result of the prolific calls for the President to show clemency by her family, prominent members of the media and a phalanx of social network supporters, but rather, her transition from prison inmate at FMC Carswell to join one of 6,694 inmates in the federal re-entry program was granted, according to her legal team, due to her having exhibited exemplary behavior while incarcerated.

The two sides of Reality Winner’s coin

To many, Reality Winner is the victim and not the insider who broke trust with her government. The government had placed their trust in her by deign of her having been issued a national security clearance. The victim side of the equation notes how the nation became more knowledgeable of Russian activities with respect to the U.S. elections and championed Winner as a “whistleblower.”

To others, she is an insider who opted to reveal to The Intercept a highly classified briefing which she printed, shoved into her pantyhose, and secreted out of the classified environment. The brief detailed the clandestine efforts being undertaken by the U.S. intelligence community to penetrate, garner additional information, and thwart Russian intelligence activities with respect to the U.S. elections. To those whose position requires them to safeguard the nation, she is viewed as a criminal, as her efforts not only had a deleterious effect on the active operational activity of the United States vis-à-vis Russia, it set those efforts back to square one.

Perhaps no one would have known of Reality Winner had The Intercept not published the content of the NSA classified brief and contacted the NSA to determine if the document they had received in the mail was authentic. The forensic exam of a controlled document by the NSA followed and a finite number of individuals had printed out the document, with Winner being one of those individuals. No sophisticated sleuthing required.

Reality Winner and her 63-month sentence

Much has been said and written about Winner’s sentence of 63 months as being out of line with others who have committed similar crimes, to include sharing classified information with The Intercept. They are correct; her sentence of 63 months was noticeably longer than that which DIA officer Frese, and CIA officers Jeffrey Sterling or John Kiriakou received. All three received sentences of 30 months for sharing classified information with media.

FBI special agent, Terry Albury was sentenced to 48 months in prison for sharing classified information with the same publication as Winner, The Intercept. While Albury didn’t secret the classified information out of the building in his shorts, he did opt to use his smartphone and photographed screen shots of the classified material so that he wouldn’t leave a paper trail for any investigators.

Many contend the discrepancy between Winner and others is that the DOJ wished to make an example of Winner. It is true she was facing a potential 120 months and fines of up to $250,000 being charged under the Espionage Act (as were the aforementioned individuals). The Bureau of Prisons guidelines calculated her crime may warrant a sentence of 87-108 months. Winner was sentence by the judge to a prison term for the precise number of months and at the prison which had been negotiated on her behalf by her own defense team. The judge had the authority to add more, subtract to make it less and opted to accept what had been negotiated. Were Winner’s attorneys at that time not as skilled as those of Frese, Sterling, Kiiriakou or Albury in negotiating a more reasonable 30-36 month sentence?

With her release, Winner will have served approximately 58 months of her 63 months and has now moved into the three years of supervised release phase of her sentence, a sentence which she received when she pleaded guilty to leaking a single document containing national defense information.




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Christopher Burgess (@burgessct) is an author and speaker on the topic of security strategy. Christopher, served 30+ years within the Central Intelligence Agency. He lived and worked in South Asia, Southeast Asia, the Middle East, Central Europe, and Latin America. Upon his retirement, the CIA awarded him the Career Distinguished Intelligence Medal, the highest level of career recognition. Christopher co-authored the book, “Secrets Stolen, Fortunes Lost, Preventing Intellectual Property Theft and Economic Espionage in the 21st Century” (Syngress, March 2008). He is the founder of